JPH05239071A - Organosilicon compound - Google Patents

Organosilicon compound

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Publication number
JPH05239071A
JPH05239071A JP4190788A JP19078892A JPH05239071A JP H05239071 A JPH05239071 A JP H05239071A JP 4190788 A JP4190788 A JP 4190788A JP 19078892 A JP19078892 A JP 19078892A JP H05239071 A JPH05239071 A JP H05239071A
Authority
JP
Japan
Prior art keywords
formula
compound according
compound
group
value
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
JP4190788A
Other languages
Japanese (ja)
Other versions
JP2865489B2 (en
Inventor
James Mcvie
ジェイムズ・マクヴィー
Martin Rowlands
マーティン・ロウランズ
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Dow Silicones UK Ltd
Original Assignee
Dow Corning Ltd
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Publication of JPH05239071A publication Critical patent/JPH05239071A/en
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/373—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
    • C11D3/3738—Alkoxylated silicones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0834—Compounds having one or more O-Si linkage
    • C07F7/0838—Compounds with one or more Si-O-Si sequences
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/04—Polysiloxanes
    • C08G77/045—Polysiloxanes containing less than 25 silicon atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/54—Silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
    • C08L83/04—Polysiloxanes
    • C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/162—Organic compounds containing Si
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/37—Polymers
    • C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C11D3/373—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
    • C11D3/3742—Nitrogen containing silicones
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
    • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
    • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
    • D06M15/65—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing epoxy groups

Abstract

PURPOSE: To obtain a new organosilicon compd. superior in wash-endurance and useful as a softener, etc., for fabric or textile.
CONSTITUTION: The compd. of formula I [wherein R is a C1-6 alkyl; R1 is an epoxy bound to Si via bivalent alkylene or alkyleneoxy; R2 to R4 are each R1, -(CH2)3O(C2H4O)x(C3H6O)yR5 (x and y are each not more than 50; R5 is H, a C1-6 alkyl, -OH, -OCH3, or -OCOCCH3), respectively; provided that R4 may be -(CH2)3(CH2)zCH3 (z is 3 to 14)], is obtd. by, e.g. reacting a compd. of formula III obtd. from a compd. of formula II as the starting material, with a compd. of formula IV.
COPYRIGHT: (C)1993,JPO

Description

【発明の詳細な説明】Detailed Description of the Invention

【０００１】[0001]

【産業上の利用分野】本発明は、ケイ素原子に結合した
エポキシ基を有する新規なオルガノシリコン化合物に関
するものである。本発明の化合物は、例えばアミノ官能
材料のための分枝剤として有用である。FIELD OF THE INVENTION The present invention relates to a novel organosilicon compound having an epoxy group bonded to a silicon atom. The compounds of the present invention are useful, for example, as branching agents for amino-functional materials.

【０００２】[0002]

【従来の技術および課題】多くの欧州国において、布帛
および織物工場の排水から出る界面活性剤およびその他
の材料の量や、さらにその環境への影響に対する懸念が
増加していきている。まさにその性質により、ほとんど
の界面活性剤は、水に分散可能であり、これらは布帛や
他の物質とその上で結合しないため、布帛を洗浄すると
容易に溶解する。一つの解決法としては、布帛または他
の物質とその上で化学的に結合可能な官能基を有する界
面活性剤を使用することである。従来の技術において、
処理される材料への“柔軟”効果の付与を含む様々な目
的のため、織物および布帛の処理にアミノ官能オルガノ
シリコン化合物を使用することがよく知られている。こ
のような処理は、例えば、1979年７月25日の日付の英国
特許第1,549,180号明細書や1991年３月19日の日付の米
国特許第5,000,861号明細書に記載されている。線状ア
ミノ官能シロキサン類を含むエマルジョンは、織物およ
び布帛に柔軟性を付与するために使用されているが、こ
のような処理は、アミノ官能シロキサンの長期耐久性が
幾分か不足するので、弾性状の仕上げにより得られる風
合いが提供されないという不利が生じる。さらに、この
エマルジョンを織物または布帛に適用した後、エマルジ
ョンからの物質、例えば界面活性剤は、洗浄時自然に取
り除かれるので、処分の求められる化学排水の別の成分
となる。BACKGROUND OF THE INVENTION In many European countries, there is increasing concern about the amount of surfactants and other materials discharged from the effluent of fabric and textile factories, and their environmental impact. By its very nature, most surfactants are dispersible in water, and they do not bind to the fabric or other substances thereover, so that the fabric is easily dissolved when washed. One solution is to use a surfactant that has functional groups that can be chemically bound to the fabric or other material. In the conventional technology,
It is well known to use amino-functional organosilicon compounds in the treatment of textiles and fabrics for a variety of purposes, including imparting a "softening" effect to the material being treated. Such treatments are described, for example, in British Patent 1,549,180 dated July 25, 1979 and US Pat. No. 5,000,861 dated March 19, 1991. Emulsions containing linear amino-functional siloxanes have been used to impart softness to textiles and fabrics, but such treatments result in some lack of long-term durability of amino-functional siloxanes, resulting in elasticity. The disadvantage is that the texture obtained by the textured finish is not provided. Furthermore, after applying this emulsion to textiles or fabrics, substances from the emulsion, such as surfactants, are naturally removed during washing and thus become another component of the chemical wastewater that requires disposal.

【０００３】[0003]

【課題を解決するための手段】本発明者らは、線状のア
ミノ官能シロキサンと、ケイ素原子に結合したエポキシ
基を有する選択されたオルガノシリコン化合物を含むエ
マルジョンを用いることにより、改善された耐久性の仕
上がり品を製造することができることを見いだした。エ
ポキシ官能オルガノシリコン化合物は従来技術において
新規ではないが（例えば1960年５月４日の日付の英国特
許第834,326号明細書および1969年１月22日の日付の英
国特許第1,140,536号明細書参照）、従来技術は、本発
明のポリシロキサン類の構造を教示してはいない。We have improved durability by using an emulsion containing a linear amino-functional siloxane and a selected organosilicon compound having an epoxy group bonded to a silicon atom. It has been found that it is possible to produce a finished product of sex. Epoxy-functional organosilicon compounds are not new in the prior art (see, for example, British Patent No. 834,326 dated May 4, 1960 and British Patent No. 1,140,536 dated January 22, 1969). , The prior art does not teach the structure of the polysiloxanes of the present invention.

【０００４】本発明はその一つの見地において、式The invention, in one of its aspects, is represented by the formula

【０００５】[0005]

【化４】 [Chemical 4]

【０００６】（式中、Ｒは１〜６個の炭素原子をもつア
ルキル基であり、Ｒ1は２価のアルキレンまたはアルキ
レンオキシ基によってケイ素原子に結合したエポキシ基
でありおよびＲ2、Ｒ3、Ｒ4はそれぞれＲ1、あるいは分
子中にオキシエチレン、場合によりオキシプロピレン単
位をもち且つ式−（ＣＨ2）3Ｏ（Ｃ2Ｈ4Ｏ）ｘ（Ｃ3Ｈ6
Ｏ）ｙＲ5（式中、ｘおよびｙはそれぞれ約５０以下の
値をもつ整数であり、Ｒ5は水素、１〜約６個の炭素原
子を有するアルキル基、−ＯＨ、−ＯＣＨ3および−Ｏ
ＣＯＣＣＨ3からなる群から選択された基である）を有
するポリオキシアルキル化置換基であり；ただしＲ4は
−（ＣＨ2）3（ＣＨ2）ｚＣＨ3（式中、ｚは３〜１４の
値をもつ整数である）であることができる）を有する化
合物を提供するものである。Wherein R is an alkyl group having 1 to 6 carbon atoms, R 1 is an epoxy group bonded to the silicon atom by a divalent alkylene or alkyleneoxy group, and R 2 , R 3 , R 4 each have R 1 or oxyethylene in the molecule, optionally an oxypropylene unit and have the formula — (CH 2 ) 3 O (C 2 H 4 O) x (C 3 H 6
O) yR 5 (wherein, x and y are integers each having a value of about 50 or less, R 5 is hydrogen, an alkyl group having 1 to about 6 carbon atoms, —OH, —OCH 3 and — O
COCCH 3 is a group selected from the group consisting of COCCH 3 ); wherein R 4 is — (CH 2 ) 3 (CH 2 ) zCH 3 (where z is 3-14). Which can be an integer with a value).

【０００７】２つ以上のＲ1基を含む本発明の化合物
は、アミノ官能シロキサンとの反応して架橋した生成物
を得ることができる。好適な化合物は、１分子につきエ
ポキシ基を約５〜約２２重量％有するものである。本発
明の化合物は、ハイドロシリレーション触媒の存在下、
対応するシランと不飽和エポキサイド、例えばアリルグ
リシジルエーテルとのハイドロシリレーション反応によ
り製造することができる。The compounds of the present invention containing more than one R 1 group can be reacted with aminofunctional siloxanes to give crosslinked products. Preferred compounds are those having from about 5 to about 22 weight percent epoxy groups per molecule. The compound of the present invention, in the presence of a hydrosilylation catalyst,
It can be prepared by the hydrosilylation reaction of the corresponding silane with an unsaturated epoxide, such as allyl glycidyl ether.

【０００８】本発明の化合物は、好ましくは、ポリオキ
シアルキル化置換基および／または脂肪基−（ＣＨ2）3
（ＣＨ2）ｚＣＨ3（式中、ｚは３〜１４の値をもつ）を
有することができる。このポリオキシアルキル化置換基
は、化合物に親水性特性を付与するが、脂肪基は疎水性
特性を付与する。従って、界面活性剤特性をもち且つ好
適な反応性材料、例えばアミノ官能シロキサンと反応
し、結合できる化合物を調製することができる。このよ
うに、本発明の化合物は、活性部位を有し且つアミノ官
能柔軟性付与組成物に添加したとき、硬化して改善され
た耐久性の仕上がり品が得られる有利さを提供するもの
である。本発明の好適な化合物は、柔軟性付与組成物の
アミノ基と反応して、洗い流されない架橋網状構造を提
供するものである。化合物の個々の種類としては、
Ｒ2、Ｒ3、およびＲ4がそれぞれＲ1であり、Ｒ2がＲ1の
場合には、Ｒ3が単位ｘが７〜１８の値を有し且つｙが
０であるポリアルキル化置換基であり、Ｒ4が−（Ｃ
Ｈ2）3（ＣＨ2）ｚＣＨ3であるものとして提供される。
この化合物は２５℃での測定で、約５０〜約２０００セ
ンチストークスの粘度を有し、この範囲において高い粘
度であると化合物はワックス状材料となる。The compounds of the invention are preferably polyoxyalkylated substituents and / or fatty groups-(CH 2 ) 3
It can have (CH 2 ) zCH 3 where z has a value of 3-14. The polyoxyalkylated substituent imparts hydrophilic character to the compound, while the fatty group imparts hydrophobic character. Thus, compounds having surfactant properties and capable of reacting and binding with suitable reactive materials such as amino-functional siloxanes can be prepared. Thus, the compounds of the present invention provide the advantage of having active sites and, when added to an amino-functional softening composition, cure to give a finished product with improved durability. .. Preferred compounds of the present invention are those that react with the amino groups of the softening composition to provide a cross-linked network that is not washed away. For each type of compound,
When R 2 , R 3 and R 4 are each R 1 , and R 2 is R 1 , a polyalkylated substitution in which R 3 has a value of unit x from 7 to 18 and y is 0 And R 4 is-(C
H 2 ) 3 (CH 2 ) zCH 3 is provided.
This compound has a viscosity of from about 50 to about 2000 centistokes, measured at 25 ° C., at high viscosities in this range the compound becomes a waxy material.

【０００９】他の見地において、本発明は、本発明の化
合物とアミノ官能ポリシロキサンとの組み合わせを含有
する組成物を提供するものである。この組成物は水性エ
マルジョンとすることができ、アミノ官能ポリシロキサ
ンは織物および布帛処理組成物に用いられる公知のもの
とすることができる。好適なアミノ官能ポリシロキサン
は、一般式In another aspect, the invention provides a composition containing a combination of a compound of the invention and an aminofunctional polysiloxane. The composition can be an aqueous emulsion and the amino-functional polysiloxane can be any of those known for use in textile and fabric treatment compositions. Suitable amino-functional polysiloxanes have the general formula

【００１０】[0010]

【化５】 [Chemical 5]

【００１１】（式中、Ｒは炭化水素基、さらに好ましく
は１〜６個の炭素原子をもつアルキル基であり、ｍは５
０〜５０００の値を有し、ｎは１〜２５の値を有する）
で表されるものである。アミノ官能シロキサンおよび本
発明の化合物を含む組成物は、織物に適用することがで
き、好ましくは触媒の存在下、例えば約８０〜１００℃
に加熱することにより織物上で反応を起こすことができ
る。Wherein R is a hydrocarbon group, more preferably an alkyl group having 1 to 6 carbon atoms, and m is 5
Has a value of 0-5000 and n has a value of 1-25)
It is represented by. The composition comprising the amino-functional siloxane and the compound of the present invention can be applied to textiles, preferably in the presence of a catalyst, eg about 80-100 ° C.
The reaction can take place on the fabric by heating to

【００１２】本発明をさらに明確にするために、本発明
の材料の例およびその調製方法を以下に記載する。表Ｉ
および表IIは、本発明に従って調製したＡ〜Ｍまでの１
２の化合物を示している。表Ｉにおいて、Ｒ1、Ｒ2、Ｒ
3およびＲ4は、上記の式に示された基に相当する。表II
は、化合物Ａ〜Ｍの幾つかの性質を示している。表Ｉお
よび表IIに続く例は、表ＩおよびIIに示された幾つかの
化合物をどのようにして調製したのか、さらにアミノポ
リシロキサンの改質剤としての化合物をどのようにして
使用したのかを示している。To further clarify the invention, examples of materials of the invention and their method of preparation are described below. Table I
And Table II shows 1 to A to M prepared according to the present invention.
Two compounds are shown. In Table I, R 1 , R 2 , R
3 and R 4 correspond to the groups shown in the above formula. Table II
Show some properties of compounds A-M. The examples following Table I and Table II show how some of the compounds shown in Tables I and II were prepared and how the compounds were used as modifiers of aminopolysiloxanes. Is shown.

【００１３】[0013]

【表１】 [Table 1]

【００１４】“ＥＯ”は、ポリエチレンオキサイド基−
（ＣＨ2）3（ＯＣ2Ｈ4）ｘＯＨ（式中、ｘは７、１２ま
たは１８である）を意味する。“Ｃ８”、“Ｃ１２”、
“Ｃ１４、“Ｃ１６”および“Ｃ１８”は、アルキル基
（ＣＨ2）3（ＣＨ2）ｚＣＨ3（式中、ｚは４、８、１
０、１２または１４である）を意味する。"EO" is a polyethylene oxide group-
It means (CH 2 ) 3 (OC 2 H 4 ) xOH, where x is 7, 12 or 18. "C8", "C12",
“C14,“ C16 ”and“ C18 ”are alkyl groups (CH 2 ) 3 (CH 2 ) zCH 3 (wherein z is 4, 8, 1
0, 12 or 14).

【００１５】[0015]

【表２】 [Table 2]

【００１６】多官能シリコーン架橋剤は、以下の手順に
従って調製することができる：The polyfunctional silicone crosslinker can be prepared according to the following procedure:

【００１７】[0017]

【化６】 [Chemical 6]

【００１８】[0018]

【実施例】以下の実施例は、本発明を説明するために記
載したものである。実施例 １ 還流器を備えたフラスコに、アリルグリシジルエーテル
２００g、塩化白金酸（Ｈ2ＰｔＣｌ6）７０μlおよび酢
酸ナトリウム（ＮａＯＡｃ）０.２gを加えた。フラスコ
を１２０℃に加熱した。テトラメチルジシロキサンとテ
トラエトキシシランとの反応からの平衡生成物であるテ
トラキス（ジメチルシロキシ）シランＳｉ（ＯＳｉＭｅ
2Ｈ）4化合物７１.８gを６時間かけてゆっくりとフラス
コに添加した。Ｓｉ（ＯＳｉＭｅ2Ｈ）4の添加完了時、
この反応をＩＲによりモニターした。反応はゆっくりと
進行した。さらに触媒の塩化白金酸７０μlを加えた。
１２時間後、ストリップした後、製造物を分離したとこ
ろ、上記の表ＩおよびIIに示される化合物“Ａ”である
テトラエポキシ官能シロキサンであると認められた。こ
の化合物は、４つの有効なエポキシ基を有し、これはそ
れぞれ反応を起こす部位を提供するものである。この化
合物は、アミノ官能オルガノシリコン化合物を用いる織
物および布帛処理の洗浄耐久性を増加させるものである
ため、布帛処理に有用である。EXAMPLES The following examples are provided to illustrate the present invention. Example 1 To a flask equipped with a reflux condenser, 200 g of allyl glycidyl ether, 70 μl of chloroplatinic acid (H 2 PtCl 6 ) and 0.2 g of sodium acetate (NaOAc) were added. The flask was heated to 120 ° C. Tetrakis (dimethylsiloxy) silane Si (OSiMe), an equilibrium product from the reaction of tetramethyldisiloxane with tetraethoxysilane.
71.8 g of 2 H) 4 compound was slowly added to the flask over 6 hours. Upon completion of addition of Si (OSiMe 2 H) 4 ,
The reaction was monitored by IR. The reaction proceeded slowly. Further, 70 μl of chloroplatinic acid as a catalyst was added.
After 12 hours, after stripping, the product was separated and identified as the compound "A" shown in Tables I and II above, a tetraepoxy functional siloxane. This compound has four available epoxy groups, each providing a site for reaction. This compound is useful in fabric treatment because it increases the wash durability of fabric and fabric treatments using amino-functional organosilicon compounds.

【００１９】実施例 ２ ディーン／スターク（Dean／Stark）装置を備えたフラ
スコに、アリルポリオキシエチレングリコールＣＨ2Ｃ
ＨＣＨ2（ＯＣＨ2ＣＨ2）18ＯＨ １５０g、トルエン４
５gおよびテトラキス（ジメチルシロキシ）シランＳｉ
（ＯＳｉＭｅ2Ｈ）4化合物５４.５gを添加した。この内
容物をディーン／スターク装置を用いて乾燥し、このフ
ラスコを９０℃に冷却した。フラスコに、塩化白金酸
（Ｈ2ＰｔＣｌ6）１００μlおよび酢酸ナトリウム（Ｎ
ａＯＡｃ）０.２５g添加し、反応を２時間還流させて行
った。フラスコを室温まで冷却した。このフラスコに、
アルケン１−ヘキサデセン３４.５gを２時間かけて加
え、フラスコをさらに２時間還流させた。フラスコを再
度室温まで冷却させた。第２のフラスコに、アリルグリ
シジルエーテル５７gを加え、この第２フラスコを１２
０〜１３０℃に加熱した。第１のフラスコの内容物を第
２フラスコに２時間かけて加えた。さらに１−ヘキサデ
センの１０gを第２フラスコに加え、フラスコを冷却
し、濾過し、溶媒がストリップしたとき生成物を分離し
た。この生成物は表ＩおよびIIに示される化合物“Ｌ”
であると認められた。 Example 2 A flask equipped with a Dean / Stark apparatus was charged with allyl polyoxyethylene glycol CH 2 C.
HCH 2 (OCH 2 CH 2 ) 18 OH 150 g, toluene 4
5 g and tetrakis (dimethylsiloxy) silane Si
54.5 g of (OSiMe 2 H) 4 compound was added. The contents were dried using a Dean / Stark apparatus and the flask was cooled to 90 ° C. In a flask, 100 μl of chloroplatinic acid (H 2 PtCl 6 ) and sodium acetate (N
0.25 g of aOAc) was added and the reaction was refluxed for 2 hours. The flask was cooled to room temperature. In this flask,
34.5 g of alkene 1-hexadecene was added over 2 hours and the flask was refluxed for another 2 hours. The flask was allowed to cool to room temperature again. To the second flask, 57 g of allyl glycidyl ether was added and the second flask was added to 12
Heated to 0-130 ° C. The contents of the first flask were added to the second flask over 2 hours. Further 10 g of 1-hexadecene was added to the second flask, the flask was cooled, filtered and the product separated when the solvent was stripped. This product is the compound "L" shown in Tables I and II.
Was accepted.

【００２０】実施例３〜６ 実施例３においてはアルケン１−オクテン１７.３gを使
用した；実施例４においてはアルケン１−デセン２５.
９gを使用した；実施例５においてはアルケン１−テト
ラデセン３０.２gを使用した；および実施例６において
はアルケン１−デセン２１.６gを使用した；こと以外
は、実施例２を繰り返した。表ＩおよびIIにおいて、実
施例３の方法に従って形成された化合物は、“Ｈ”とし
て示される。実施例５の方法に従って形成された化合物
は“Ｋ”であり、表ＩおよびIIに示されている。実施例
４および６の方法に従って形成された化合物は、表Ｉお
よびIIに示していないが、化合物はＲ4基の炭素原子数
を除いて、生成物“Ｈ”“Ｋ”および“Ｌ”と構造的に
同様であった。 Examples 3-6 In Example 3, 17.3 g of alkene 1-octene was used; in Example 4 alkene 1-decene 25.
Example 2 was repeated except that 9 g was used; in Example 5 30.2 g of alkene 1-tetradecene was used; and in Example 6 21.6 g of alkene 1-decene was used. In Tables I and II, the compound formed according to the method of Example 3 is designated as "H". The compound formed according to the method of Example 5 is "K" and is shown in Tables I and II. The compounds formed according to the methods of Examples 4 and 6 are not shown in Tables I and II, except that the compounds are labeled as products "H""K" and "L", except for the number of carbon atoms in the R 4 group. It was structurally similar.

【００２１】実施例 ７ 圧力均等ロート（pressure equalising funnel）、凝縮
器、温度計および空気制御撹拌器を備えた３つ首２５０
ml容丸底フラスコに、Ｓｉ（ＯＳｉＭｅ2Ｈ）4（２０
g、０.２４モルＳｉＨ）、アリルポリエーテル（０.０
６モル）、酢酸ナトリウム（０.１g）およびトルエン
（２５g）を充填した。圧力均等ロートにアルケンを充
填した。この混合物を９０℃に加熱し、塩化白金酸溶液
（２５ml）を添加した。この混合物を１２０℃に加熱
し、１時間後、アルケン（０.０６モル）をロートから
滴下した。混合物をさらに１時間、１２０℃に維持し、
続いて雰囲気温度に冷却した。圧力均等ロート、凝縮
器、温度計および空気撹拌器を備えた第２の２５０ml容
丸底フラスコに、アリルグリシジルエーテル（２０.５
５g、０.１８モル）および塩化白金酸溶液（１０ml）を
充填した。この第１フラスコの内容物を第２フラスコ上
の圧力均等ロートに移した。アリルグリシジルエーテル
を１２０℃に加熱し、ロートの内容物をフラスコに滴下
して加えた。添加が終了したとき、混合物を１２０℃で
３時間加熱した。フラスコを雰囲気温度に冷却し、ダイ
カライトの充填床を通して濾過し、トルエンと過剰のア
リルグリシジルエーテルを真空下除去した。各試験で用
いたアリルグリシジルエーテルおよびアルケンの量を表
IIIに示す。 Example 7 Three neck 250 with pressure equalizing funnel, condenser, thermometer and air controlled agitator.
In a ml round bottom flask, add Si (OSiMe 2 H) 4 (20
g, 0.24 mol SiH), allyl polyether (0.0
6 mol), sodium acetate (0.1 g) and toluene (25 g) were charged. A pressure equalizing funnel was filled with alkenes. The mixture was heated to 90 ° C. and chloroplatinic acid solution (25 ml) was added. The mixture was heated to 120 ° C. and after 1 hour alkene (0.06 mol) was added dropwise from the funnel. The mixture is kept at 120 ° C. for another hour,
Then it was cooled to ambient temperature. In a second 250 ml round bottom flask equipped with a pressure equalizing funnel, condenser, thermometer and air stirrer, allyl glycidyl ether (20.5
5 g, 0.18 mol) and chloroplatinic acid solution (10 ml) were charged. The contents of this first flask were transferred to a pressure equalizing funnel on the second flask. Allyl glycidyl ether was heated to 120 ° C. and the contents of the funnel were added dropwise to the flask. When the addition was complete, the mixture was heated at 120 ° C. for 3 hours. The flask was cooled to ambient temperature, filtered through a packed bed of dicalite and the toluene and excess allyl glycidyl ether removed under vacuum. Show the amounts of allyl glycidyl ether and alkenes used in each test.
Shown in III.

【００２２】[0022]

【表３】 [Table 3]

【００２３】実施例 ８ アミン官能ポリシロキサンのための反応性界面活性剤と
して、アミン官能ポリシロキサン１５部、本発明の化合
物９部、酢酸０.２５部および水７５.７５部を含むエマ
ルジョンを調製することにより、表ＩおよびIIの化合物
を試験した。各化合物をアミン官能ポリシロキサンおよ
び酢酸と混合し、１６時間、８０℃に加熱した。この生
成物は、軟らかいゲルからゴム状のゲルの生成物を形成
し始める白色のエマルジョンを形成し、本発明の化合物
は、この生成物をアミノシリコーン布帛用柔軟剤エマル
ジョンシステムに有用とする反応性シロキサンとして機
能可能であることを示した。本発明の化合物は、アミノ
シリコーン材料と架橋された網状構造を形成する。この
実施例に従って試験されたアミン官能ポリシロキサン
は、公知の市販されている材料であり、式 EXAMPLE 8 An emulsion containing 15 parts of an amine functional polysiloxane, 9 parts of a compound of the invention, 0.25 part of acetic acid and 75.75 parts of water as a reactive surfactant for an amine functional polysiloxane is prepared. The compounds of Tables I and II were tested by Each compound was mixed with amine functional polysiloxane and acetic acid and heated to 80 ° C. for 16 hours. This product forms a white emulsion that begins to form a rubbery gel product from a soft gel, and the compounds of the present invention make the product useful in aminosilicone fabric softener emulsion systems. It has been shown that it can function as a siloxane. The compounds of the present invention form a crosslinked network with aminosilicone materials. The amine functional polysiloxanes tested according to this example are known, commercially available materials of the formula

【００２４】[0024]

【化７】 [Chemical 7]

【００２５】（式中、Ｍｅはメチルを示し、ｍは５０〜
５０００の値をもつ整数であり、ｎは１〜１２５の値を
もつ整数である）を有する。これらのアミン官能ポリシ
ロキサンのアミンのモル％は、約０.６〜２.３で変化し
た。他の多くの変更および改良は、本発明の本質的な性
質および概念を逸脱しない限り、ここに記載された構
造、化合物、組成物および方法によってなすことができ
ることが、上記から明らかである。従って、ここに記載
された本発明の態様は、単なる例示であり、本発明の範
囲を限定するためのものではないことが明らかに理解で
きる。(In the formula, Me represents methyl, and m is 50 to 50).
Is an integer with a value of 5000 and n is an integer with a value of 1-125). The amine mole percent of these amine functional polysiloxanes varied from about 0.6 to 2.3. It will be apparent from the above that many other changes and modifications can be made with the structures, compounds, compositions and methods described herein without departing from the essential nature and concept of the invention. Therefore, it can be clearly understood that the embodiments of the invention described herein are merely illustrative and are not intended to limit the scope of the invention.

フロントページの続き (72)発明者 マーティン・ロウランズ イギリス国、ウェイルズ、ウエスト・グラ モーガン、ニース、キムラ・ロード 106Front Page Continuation (72) Inventor Martin Lowlands England, Wales, West Glamorgan, Nice, Kimura Road 106

Claims (11)

【特許請求の範囲】[Claims] 【請求項１】 式 【化１】 ［式中、Ｒは１〜６個の炭素原子をもつアルキル基であ
り、Ｒ1は２価のアルキレンまたはアルキレンオキシ基
によってケイ素原子に結合したエポキシ基であり、およ
びＲ2、Ｒ3、Ｒ4は、それぞれＲ1、あるいは分子中にオ
キシエチレン、場合によりオキシプロピレン単位を有
し、且つ式−（ＣＨ2）3Ｏ（Ｃ2Ｈ4Ｏ）ｘ（Ｃ3Ｈ6Ｏ）
ｙＲ5（式中、ｘおよびｙはそれぞれ約５０以下の値を
もつ整数であり、Ｒ5は水素、１〜約６個の炭素原子を
有するアルキル基、−ＯＨ、−ＯＣＨ3および−ＯＣＯ
ＣＣＨ3からなる群から選択された基である）を有する
ポリオキシアルキル化置換基であり；ただしＲ4は−
（ＣＨ2）3（ＣＨ2）ｚＣＨ3（式中、ｚは３〜１４の値
をもつ整数である）であることができる］を有するオル
ガノシリコン化合物。1. The formula: [Wherein R is an alkyl group having 1 to 6 carbon atoms, R 1 is an epoxy group bonded to a silicon atom by a divalent alkylene or alkyleneoxy group, and R 2 , R 3 , R 4 each have R 1 , or oxyethylene in the molecule, optionally an oxypropylene unit, and have the formula — (CH 2 ) 3 O (C 2 H 4 O) x (C 3 H 6 O)
yR 5 (wherein, x and y are integers each having a value of about 50 or less, R 5 is hydrogen, an alkyl group having 1 to about 6 carbon atoms, —OH, —OCH 3 and —OCO).
CCH 3 is a group selected from the group consisting of) be a polyoxyalkylated substituent having; provided R 4 is -
An organosilicon compound having (CH 2 ) 3 (CH 2 ) zCH 3 (wherein z can be an integer having a value of 3 to 14). 【請求項２】 エポキシ基が、 【化２】 である、請求項１に記載の化合物。2. An epoxy group is represented by: The compound of claim 1, which is 【請求項３】 Ｒ2、Ｒ3およびＲ4がそれぞれ請求項１
で定義されたＲ1である、請求項１または２に記載の化
合物。3. R 2 , R 3 and R 4 are each claim 1.
A compound according to claim 1 or 2 which is R 1 as defined in. 【請求項４】 Ｒ2、Ｒ3およびＲ4の内の一つが請求項
１で定義されたＲ1である、請求項１または２に記載の
化合物。Wherein one of R 2, R 3 and R 4 are R 1 defined in claim 1 A compound according to claim 1 or 2. 【請求項５】 Ｒ2、Ｒ3およびＲ4の内の一つが請求項
１で定義されたポリオキシアルキル化置換基である請求
項１、２、４のいずれか１項に記載の化合物。5. A compound according to any one of claims 1, 2 and 4 wherein one of R 2 , R 3 and R 4 is a polyoxyalkylated substituent as defined in claim 1. 【請求項６】 ｘが７〜１８の値を有し且つｙが０であ
る、請求項５に記載の化合物。6. A compound according to claim 5, wherein x has a value of 7-18 and y is 0. 【請求項７】 Ｒ2、Ｒ3およびＲ4の内の一つが、請求
項１で定義された−（ＣＨ2）3（ＣＨ2）ｚＣＨ3基であ
る、請求項１、２、４、５、６のいずれか１項に記載の
化合物。7. One of R 2 , R 3 and R 4 is a — (CH 2 ) 3 (CH 2 ) zCH 3 group as defined in claim 1, 2. The compound according to any one of 5 and 6. 【請求項８】 ２５℃で約５０〜２０００センチストー
クスの粘度をもつ、請求項１ないし７のいずれか１項に
記載の化合物。8. A compound according to any one of claims 1 to 7 having a viscosity of about 50-2000 centistokes at 25 ° C. 【請求項９】 ワックス状の材料である、請求項１ない
し７のいずれか１項に記載の化合物。9. The compound according to claim 1, which is a waxy material. 【請求項１０】 アミン官能ポリシロキサンと、請求項
１ないし９のいずれか１項に記載の化合物の併用を含
む、組成物。10. A composition comprising a combination of an amine functional polysiloxane and a compound according to any one of claims 1-9. 【請求項１１】 アミン官能ポリシロキサンが、式 【化３】 （式中、Ｒは炭素原子１〜６個をもつアルキル基であ
り、ｍは５０〜５０００の値を有し、ｎは１〜１２５の
値を有する）を有する、請求項１０に記載の組成物。11. The amine functional polysiloxane has the formula: 11. The composition according to claim 10, having the formula: wherein R is an alkyl group having 1 to 6 carbon atoms, m has a value of 50 to 5000 and n has a value of 1 to 125. object.
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JP4880588B2 (en) * 2004-04-12 2012-02-22 ダウ・コーニング・コーポレイション Personal care products
WO2014069545A1 (en) * 2012-10-30 2014-05-08 デクセリアルズ株式会社 Novel epoxy group-containing siloxane compound
JP2014111707A (en) * 2012-10-30 2014-06-19 Dexerials Corp Novel epoxy group-containing siloxane compound

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CA2074059A1 (en) 1993-01-19
GB9115592D0 (en) 1991-09-04
EP0523910B1 (en) 1996-11-20
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CA2074059C (en) 1999-01-05
DE69215285D1 (en) 1997-01-02

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